To synthesize a Ugi Product following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 38 in the DEXP014-V1B file from D-EXP014 .The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.
No dissolution could be achieved during the additions even with 30 minutes of vortexing as well as further dilution.
Conclusion
Experiment aborted because a clear solution was never obtained immediately after mixing all reagents or the addition of extra solvent. A further discussion of the apparent amine selective solubility of phenanthrene-9-carboxaldehyde is presented here.
Log
2008-02-28
15:46- Weighed out the Phenanthrene-9-carboxaldehyde.
15:52- Weighed out the phenylacetic acid.
15:55- Charged a vial with 1000 ul of methanol.
16:04- Added the propylamine to the vial.
16:05 Vortexed vial 1 min
16:06- Added the phenanthrene-9-carboxaldehyde.
16:07-Vortexed vial 1 min
16:08- Added the phenylacetic acid.
16:09-Vortexed vial 1 min, did not dissolve, moved on to next addition
16:10- Added the n-butyl isocyanide.
16:11-Vortexed 5 min, still no dissolution, made decision to add methanol to dilute it.
16:16-Added extra 500ul of methanol
16:17-Vortexed 5 min, still no dissolution
16:22-Added another 500ul of methanol
16:23-Vortexed 5 min, no change in solubility
16:28-Concluded that no further dissolution possible.
16:35- A photo was taken (177A) to demonstrate insolubility.
Objective
To synthesize a Ugi Product following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.This compounds was ranked 38 in the DEXP014-V1B file from D-EXP014 .The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.
Procedure
As described in Explan005This reaction used Phenanthrene-9-carboxaldehyde, propylamine, n-butyl isocyanide and phenylacetic acid.
Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR
carboxaldehyde
(density=0.719g/ml)
(density=0.795g/ml)
Density information found on the Ugi Chemicals Page in Left Navigation Bar.
Results
Photos taken directly after all the components were charged and vortexed.All results are recorded Master Table and Workflow Tables .
Discussion
No dissolution could be achieved during the additions even with 30 minutes of vortexing as well as further dilution.Conclusion
Experiment aborted because a clear solution was never obtained immediately after mixing all reagents or the addition of extra solvent. A further discussion of the apparent amine selective solubility of phenanthrene-9-carboxaldehyde is presented here.Log
2008-02-28
15:46- Weighed out the Phenanthrene-9-carboxaldehyde.15:52- Weighed out the phenylacetic acid.
15:55- Charged a vial with 1000 ul of methanol.
16:04- Added the propylamine to the vial.
16:05 Vortexed vial 1 min
16:06- Added the phenanthrene-9-carboxaldehyde.
16:07-Vortexed vial 1 min
16:08- Added the phenylacetic acid.
16:09-Vortexed vial 1 min, did not dissolve, moved on to next addition
16:10- Added the n-butyl isocyanide.
16:11-Vortexed 5 min, still no dissolution, made decision to add methanol to dilute it.
16:16-Added extra 500ul of methanol
16:17-Vortexed 5 min, still no dissolution
16:22-Added another 500ul of methanol
16:23-Vortexed 5 min, no change in solubility
16:28-Concluded that no further dissolution possible.
16:35- A photo was taken (177A) to demonstrate insolubility.
Tags
propylamine InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3 InChIKey WGYKZJWCGVVSQN-UHFFFAOYAGPhenanthrene-9-carboxaldehydeInChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H QECIGCMPORCORE-UHFFFAOYAE
phenylacetic acid InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3 WLJVXDMOQOGPHL-UHFFFAOYAR
n-butyl isocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3 InChIKey: FSBLVBBRXSCOKU-UHFFFAOYAR
Ugi Product InChI=1/C3 1H34N2O2/c1-3-5-19-32-31(35)30(33(20-4-2)29(34)21-23-13-7-6- 8-14-23)28-22-24-15-9-10-16-25(24)26-17-11-12-18-27(26)28/h6 -18,22,30H,3-5,19-21H2,1-2H3,(H,32,35) InChIKey: JNSYWEITXVHUPZ-UHFFFAOYAJ